GB634531A - New quinoline derivatives - Google Patents

New quinoline derivatives

Info

Publication number
GB634531A
GB634531A GB2332447A GB2332447A GB634531A GB 634531 A GB634531 A GB 634531A GB 2332447 A GB2332447 A GB 2332447A GB 2332447 A GB2332447 A GB 2332447A GB 634531 A GB634531 A GB 634531A
Authority
GB
United Kingdom
Prior art keywords
amino
quinaldine
nitrobenzene
methyl
give
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB2332447A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to BE484447D priority Critical patent/BE484447A/xx
Priority to NL67237D priority patent/NL67237C/xx
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB2332447A priority patent/GB634531A/en
Priority to US44236A priority patent/US2585917A/en
Priority to FR1018275D priority patent/FR1018275A/en
Priority to DEP2256A priority patent/DE825264C/en
Publication of GB634531A publication Critical patent/GB634531A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Abstract

Pyrimidylaminoquinoline derivatives of general formula Pq-NH-Qq, wherein P represents a 2-, 4- or 6-amino-substituted pyrimidine nucleus attached to the linking -NH-group at another of the 2-, 4- or 6-positions and which may be substituted in the remaining 2-, 4- or 6-positions by an alkyl radicle of not more than 5 carbon atoms or an amino group, Q stands for a quinoline nucleus substituted in the 2- or 4-position by an amino group and may be substituted by an alkyl group or groups of not more than 5 carbon atoms and contains the -NH- link in the 6-position, and the symbols q indicate that the preceding nuclei, P and Q, are present in the form of quaternary salts, are obtained by reacting one or more of the substances P-NH-Q, Pq-NH-Q and P-NH-Qq with a quaternary salt-forming agent such as dimethyl sulphate and methyl iodide and p-toluene sulphonate. The reaction may be effected by heating the reactants together conveniently in a solvent such as ethyl alcohol, acetonitrile or nitrobenzene. It is often possible and advisable in separations to convert one disalt into another thus a di-(metho-methyl sulphate) may be converted to a dimethochloride with e.g. sodium chloride. The products are trypanocides having both curative and prophylactic properties. In examples: (1) 4-amino-6-(21-amino-61-methyl-pyrimidyl - 41 - amino) - quinaldine is heated with methyl iodide in ethyl alcohol at 100-110 DEG C. to give a complex of 4-amino-6-(21-amino - 61 - methylpyrimidyl - 41 - amino)-quinaldine - 1 : 11 - dimethiodide and the corresponding 1-methiodide hydriodide which is treated with hot dil-hydrochloric acid and filtered, the solid being dissolved in sodium carbonate and sodium chloride added to yield the corresponding quinaldine-1 : 11-dimethochloride; (2) 4 - amino - 6 - (41 - amino - 61-methyl - pyrimidyl - 21 - amino) - quinaldine is heated at 115-120 DEG C. with methyl iodide in methyl alcohol to give the 1 : 11-dimethiodide; (3) 4 - amino - 6 - (21 - aminopyrimidyl - 41-amino)-quinaldine is boiled under reflux with methyl iodide and acetonitrile to give the 1 : 11-dimethiodide; (4) 4 - amino - 6 - (21 - amino-61 - methylpyrimidyl - 41 - amino) - quinaldine-11 - methiodide in nitrobenzene is heated at 100 DEG C. dimethyl sulphate added and a solid precipitated with acetone which is treated with brine to yield the required quinaldine 1 : 11-dimethochloride; (5) the quinaldine of example (1) is heated in nitrobenzene at 100 DEG C. dimethyl sulphate added and the corresponding 1 : 11-dimethomethylsulphate isolated which may be converted to the 1 : 11-dimethochloride or -dimethiodide by treatment with sodium chloride or iodide respectively; (6) 4-amino-6-(21 - amino - 61 - methylpyrimidyl - 41 - amino) quinaldine 1-methomethylsulphate in nitrobenzene at 100 DEG C. is treated with dimethyl sulphate to give the 1 : 11-dimethomethylsulphate; (7) 4 - amino - 6 - (21 - amino - 61-ethylpyrimidyl - 41 - amino) - quinaldine in nitrobenzene at 110 DEG C. is treated with dimethyl sulphate, the solid obtained treated with excess sodium iodide and the latter product crystallized from aqueous hydrochloric acid to give the desired 1 : 11-dimethochloride; (8) 4 - amino - 6 - (21 - amino - 61 - pentylpyrimidyl - 41 - amino) - quinaldine is heated with dimethyl sulphate in nitrobenzene at 120 DEG C., treated with excess water, and brine added to the aqueous alkaline extract to give the 1 : 1-dimethochloride; (9) 4-amino-6-(21 : 61 - diaminopyrimidyl - 41 - amino)-quinaldine is heated with dimethyl sulphate at 120 DEG C. in nitrobenzene and the corresponding 1 : 11-dimethiodide obtained on treating an aqueous extract with sodium iodide and in (10) 2 - amino - 6 - (21 - amino - 61 - methylpyrimidyl - 41 - amino) - lepidine is heated with methyl p-toluenesulphonate in nitrobenzene at 120 DEG C. and the solid obtained on adding acetone is treated with aqueous sodium iodide to give the 1 : 11-dimethiodide. The starting materials are obtained by condensing the appropriately substituted diaminoquinaldine or lepidine and 2-chloro- or 4-chloro-substituted pyrimidine in aqueous hydrochloric acid and precipitating the desired base with alkali. In (1) the starting compound is also obtained by refluxing 6-amino-4-hydroxy-quinaldine hydrochloride with 4-chloro-2-amino-6-methylpyrimidine treating with ammonia and separating 4 - hydroxy - 6 - (21 - amino - 61-methylpyrimidyl - 41 - amino) - quinaldine which is converted to the corresponding 4-chloro and 4-amino-compound by treatment with phosphorus oxychloride and ammonia respectively. The starting methiodide of (4) is obtained by condensing 4 : 6-diaminoquinaldine with 4 - chloro - 2 - amino - 6 - methylpyrimidine 1 - methiodide in aqueous hydrochloric and treating the 4-amino-6-(21-amino-6 - (21 - amino - 61 - methylpyrimidyl - 41-amino) - quinaldine - 11 - methiodide hydriodide thus obtained with aqueous alkali and the methosulphate of (6) is obtained by treating the free base in cold p-ethoxy-ethanol with dimethyl sulphates.
GB2332447A 1947-08-22 1947-08-22 New quinoline derivatives Expired GB634531A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BE484447D BE484447A (en) 1947-08-22
NL67237D NL67237C (en) 1947-08-22
GB2332447A GB634531A (en) 1947-08-22 1947-08-22 New quinoline derivatives
US44236A US2585917A (en) 1947-08-22 1948-08-13 Process for the manufacture of quaternary salts of pyrimidylaminoquinolines
FR1018275D FR1018275A (en) 1947-08-22 1948-08-19 Pyrimidylaminoquinoline derivatives
DEP2256A DE825264C (en) 1947-08-22 1949-03-18 Process for the preparation of diquartar salts of pyrimidylaminoquinolines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2332447A GB634531A (en) 1947-08-22 1947-08-22 New quinoline derivatives

Publications (1)

Publication Number Publication Date
GB634531A true GB634531A (en) 1950-03-22

Family

ID=10193766

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2332447A Expired GB634531A (en) 1947-08-22 1947-08-22 New quinoline derivatives

Country Status (6)

Country Link
US (1) US2585917A (en)
BE (1) BE484447A (en)
DE (1) DE825264C (en)
FR (1) FR1018275A (en)
GB (1) GB634531A (en)
NL (1) NL67237C (en)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2068824A (en) * 1937-01-26 Quaternary heterocyclic acid
US2465568A (en) * 1949-03-29 Pyrimidine compounds
US2295563A (en) * 1941-07-30 1942-09-15 Gen Electric Diazine derivatives

Also Published As

Publication number Publication date
DE825264C (en) 1951-12-17
US2585917A (en) 1952-02-19
BE484447A (en)
FR1018275A (en) 1953-01-05
NL67237C (en)

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